Lithium hydroxide, monohydrate → N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine

HRID 29051Notes

Reaction equation

HRID 29051 reaction equation
C([N:4]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:5][C:6]([O:8]CC)=[O:7])(=O)C.O[Li].O>CO.O>[CH3:25][C:24]1[O:23][N:22]=[C:21]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15870967HCID 15870967, compound

Product 1

HCID 15870965N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycineYield 69.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of N-acetyl-N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine, ethyl ester (Step 1) (0.24 g, 0.54 mmol) in methanol was added LiOH.H2O (0.06 g, 1.36 mmol) in water. After 5 days the reaction was complete and the solvents were removed in vacuo. The resulting semi-solid was partitioned between ethyl acetate and 1N KHSO4 solution. The ethyl acetate phase was dried over MgSO4, filtered and concentrated in vacuo yielding N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine (0.139 g, 69%) as a white powder: mp 242-248° C. 1H NMR (CDCl3/300 MHz with DMSO-d6) 7.76 (d, 2H, J=8.5 Hz), 7.33-7.22 (m, 5H), 7.19 (d, 2H, J=8.5 Hz), 6.35 (t, 1H, J=5.4 Hz), 3.63 (d, 2H, J=5.4 Hz), 2.39 (s, 3H). FABLRMS m/z 373 (M+H). FABHRMS m/z 372.0786 (M+, Calc'd 372.0780). Anal. Calc'd for C18H16N2O5S: C, 58.06; H, 4.33; N, 7.52. Found C, 58.09; H, 4.44; N, 7.45.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe resulting semi-solid was partitioned between ethyl acetate and 1N KHSO4 solution
  3. dry with materialThe ethyl acetate phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09f638eae9744b9798a1e54ebafd5fa2
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Reaction notes

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